European Union (EU) enlargement and the later shaping of its relationships with its new Eastern neighbours through the European Neighbourhood Policy (ENP) have had a significant impact on communities outside the EU’s borders. As the EU has sought to control flows of people, money and goods through these new borders, it has also become a destination for irregular migrants and small-scale traders from its eastern neighbours. This article draws upon participant observation in one such community in western Ukraine, where continuing levels of high unemployment and low wages and pensions drive dependence on flows of remittances from migrants to southern Europe, but also revenues from small-scale trade with neighbouring EU members, such as Romania. New forms of transnational mobility have emerged, which are not gender-neutral. The article asserts that, while hegemonic masculinities exist in both Ukrainian and Romanian communities, gender relations in Romania are restricted by sexualised discourses. As male and female Ukrainian traders interact with Romanian border officials and local distributors and intermediaries, hegemonic masculinities in Ukraine are re-affirmed and female traders are unable to advance and develop their trade in the same way as their male counterparts. In doing so, the article expands research on gender and transnationalism in post-enlargement Europe beyond migration and demonstrates not only how encounters at the EU’s borders are shaping gender relations in communities outside the EU, but that involvement in cross-border economic activities is determined by the gendered discourses and performance that take place at the border.